User menu

Synthesis and Photophysical Properties of Triazolyl IrIII Nucleosides

Bibliographic reference Passays, Johan ; Rubay, Christophe ; Marcélis, Lionel ; Elias, Benjamin. Synthesis and Photophysical Properties of Triazolyl IrIII Nucleosides. In: European Journal of Inorganic Chemistry, , p. 623-629 (2017)
Permanent URL http://hdl.handle.net/2078.1/186304
  1. Huisgen Rolf, 1,3-Dipolar Cycloadditions. Past and Future, 10.1002/anie.196305651
  2. Angew. Chem., 75, 139 (1963)
  3. Huisgen Rolf, Szeimies Günter, Möbius Leander, 1.3-Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC-Mehrfachbindungen, 10.1002/cber.19671000806
  4. Kolb Hartmuth C., Finn M. G., Sharpless K. Barry, Click Chemistry: Diverse Chemical Function from a Few Good Reactions, 10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.0.co;2-5
  5. Kolb Hartmuth C., Finn M. G., Sharpless K. Barry, Click-Chemie: diverse chemische Funktionalität mit einer Handvoll guter Reaktionen, 10.1002/1521-3757(20010601)113:11<2056::aid-ange2056>3.0.co;2-w
  6. Rostovtsev Vsevolod V., Green Luke G., Fokin Valery V., Sharpless K. Barry, A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes, 10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4
  7. Angew. Chem., 114, 1508 (2002)
  8. Tornøe Christian W., Christensen Caspar, Meldal Morten, Peptidotriazoles on Solid Phase:  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides, 10.1021/jo011148j
  9. Moses John E., Moorhouse Adam D., The growing applications of click chemistry, 10.1039/b613014n
  10. Meldal Morten, Tornøe Christian Wenzel, Cu-Catalyzed Azide−Alkyne Cycloaddition, 10.1021/cr0783479
  11. Amblard Franck, Cho Jong Hyun, Schinazi Raymond F., Cu(I)-Catalyzed Huisgen Azide−Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry, 10.1021/cr9001462
  12. Khakshoor Omid, Kool Eric T., Chemistry of nucleic acids: impacts in multiple fields, 10.1039/c1cc11021g
  13. Müller Jens, Metal-Ion-Mediated Base Pairs in Nucleic Acids, 10.1002/ejic.200800301
  14. Clever Guido H., Kaul Corinna, Carell Thomas, DNA-Metal Base Pairs, 10.1002/anie.200701185
  15. Clever Guido H., Kaul Corinna, Carell Thomas, DNA-Metall-Basenpaare, 10.1002/ange.200701185
  16. Clever Guido H., Shionoya Mitsuhiko, Metal–base pairing in DNA, 10.1016/j.ccr.2010.04.014
  17. Teo Yin Nah, Kool Eric T., DNA-Multichromophore Systems, 10.1021/cr100351g
  18. Weizman Haim, Tor Yitzhak, 2,2‘-Bipyridine Ligandoside:  A Novel Building Block for Modifying DNA with Intra-Duplex Metal Complexes, 10.1021/ja005785n
  19. Weizman Haim, Tor Yitzhak, Oligo-ligandosides: a DNA mimetic approach to helicate formation, 10.1039/b009855h
  20. Megger Nicole, Welte Lorena, Zamora Félix, Müller Jens, Metal-mediated aggregation of DNA comprising 2,2′-bipyridine nucleoside, an asymmetrically substituted chiral bidentate ligand, 10.1039/c0dt01569e
  21. Brotschi Christine, Häberli Adrian, Leumann Christian J., A Stable DNA Duplex Containing a Non-Hydrogen-Bonding and Non-Shape-Complementary Base Couple: Interstrand Stacking as the Stability Determining Factor, 10.1002/1521-3773(20010817)40:16<3012::aid-anie3012>3.0.co;2-y
  22. Brotschi Christine, Häberli Adrian, Leumann Christian J., Ein stabiler DNA-Duplex mit einem nichtwasserstoffverbrückenden, nichtformkomplementären Basenpaar: Interstrang-Stapelwechselwirkungen als stabilitätsbestimmender Faktor, 10.1002/1521-3757(20010817)113:16<3101::aid-ange3101>3.0.co;2-y
  23. Brotschi Christine, Leumann Christian J., DNA with Hydrophobic Base Substitutes: A Stable, Zipperlike Recognition Motif Based On Interstrand-Stacking Interactions, 10.1002/anie.200250516
  24. Brotschi Christine, Leumann Christian J., DNA mit hydrophobem Basen-Ersatz: ein stabiles reißverschlussartiges Erkennungsmuster durch Interstrang-Basen-Stapelwechselwirkungen, 10.1002/ange.200250516
  25. Štimac Anton, Leban Ivan, Kobe JoŽe, An Efficient Stereospecific Method for the Synthesis of 8-Aza-3-deazaguanine Nucleosides from Glycosyl Azides, 10.1055/s-1999-2755
  26. Ermolat'ev Denis S., Mehta Vaibhav Pravinchandra, Van der Eycken Erik V., Synthesis of Furo[2,3-b]pyrazine Nucleoside Analogues with 1,2,3-Triazole Linkage, 10.1002/qsar.200740123
  27. El Akri Khalid, Bougrin Khalid, Balzarini Jan, Faraj Abdesslem, Benhida Rachid, Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides, 10.1016/j.bmcl.2007.08.077
  28. Chittepu Padmaja, Sirivolu Venkata Ramana, Seela Frank, Nucleosides and oligonucleotides containing 1,2,3-triazole residues with nucleobase tethers: Synthesis via the azide-alkyne ‘click’ reaction, 10.1016/j.bmc.2008.08.026
  29. Malnuit, Synlett, 2123 (2009)
  30. Alvarez Rosa, Velazquez Sonsoles, San-Felix Ana, Aquaro Stefano, Clercq Erik De, Perno Carlo-Federico, Karlsson Anna, Balzarini Jan, Camarasa Maria Jose, 1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity, 10.1021/jm00050a015
  31. Pradere Ugo, Roy Vincent, McBrayer Tamara R., Schinazi Raymond F., Agrofoglio Luigi A., Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition, 10.1016/j.tet.2008.07.007
  32. Wilkinson Brendan L., Long Hilary, Sim Edith, Fairbanks Antony J., Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis, 10.1016/j.bmcl.2008.09.082
  33. Boritzki Theodore J., Berry David A., Besserer Judith A., Dan Cook P., Fry David W., Leopold Wilbur R., Jackson Robert C., Biochemical and antitumor activity of tiazofurin and its selenium analog (2-β-D-ribofuranosyl-4-selenazolecarboxamide), 10.1016/0006-2952(85)90617-3
  34. Lo Kenneth Kam-Wing, Chung Chi-Keung, Zhu Nianyong, Nucleic Acid Intercalators and Avidin Probes Derived from Luminescent Cyclometalated Iridium(III)–Dipyridoquinoxaline and –Dipyridophenazine Complexes, 10.1002/chem.200500885
  35. Lo Kenneth Kam-Wing, Chan Bruce Ting-Ngok, Liu Hua-Wei, Zhang Kenneth Yin, Li Steve Po-Yam, Tang Tommy Siu-Ming, Cyclometalated iridium(iii) polypyridine dibenzocyclooctyne complexes as the first phosphorescent bioorthogonal probes, 10.1039/c2cc36907a
  36. Jacques Alexandre, Kirsch-De Mesmaeker Andrée, Elias Benjamin, Selective DNA Purine Base Photooxidation by Bis-terdentate Iridium(III) Polypyridyl and Cyclometalated Complexes, 10.1021/ic402476b
  37. Shao Fangwei, Elias Benjamin, Lu Wei, Barton Jacqueline K., Synthesis and Characterization of Iridium(III) Cyclometalated Complexes with Oligonucleotides:  Insights into Redox Reactions with DNA, 10.1021/ic7014012
  38. Choi Jung-Suk, Maity Ayan, Gray Thomas, Berdis Anthony J., A Metal-containing Nucleoside That Possesses Both Therapeutic and Diagnostic Activity against Cancer, 10.1074/jbc.m114.620294
  39. Brotschi Christine, Mathis G�rald, Leumann Christian J., Bipyridyl- and Biphenyl-DNA: A Recognition Motif Based on Interstrand Aromatic Stacking, 10.1002/chem.200400858
  40. Grosshenny Vincent, Romero Francisco M., Ziessel Raymond, Construction of Preorganized Polytopic Ligands via Palladium-Promoted Cross-Coupling Reactions, 10.1021/jo962068w
  41. O’Sullivan Thomas J., Djukic Brandon, Dube Paul A., Lemaire Martin T., Preparation and properties of thienyl and 2,2′-bithienyl substituted cobalt-bis(semiquinone) valence tautomers, 10.1139/v09-012
  42. Hissler Muriel, Connick William B., Geiger David K., McGarrah James E., Lipa Donald, Lachicotte Rene J., Eisenberg Richard, Platinum Diimine Bis(acetylide) Complexes:  Synthesis, Characterization, and Luminescence Properties, 10.1021/ic991250n
  43. Ziessel Raymond, Suffert Jean, Youinou Marie-Thérèse, General Method for the Preparation of Alkyne-Functionalized Oligopyridine Building Blocks, 10.1021/jo960538g
  44. Hansen, Synlett, 3275 (2009)
  45. Plummer Edward A., Hofstraat Johannes W., De Cola Luisa, Mono- and di-nuclear iridium(iii) complexes. Synthesis and photophysics, 10.1039/b300704a
  46. King K. A., Watts R. J., Dual emission from an ortho-metalated iridium(III) complex, 10.1021/ja00239a060
  47. Cao Rui, Jia Junli, Ma Xiaochuan, Zhou Ming, Fei Hao, Membrane Localized Iridium(III) Complex Induces Endoplasmic Reticulum Stress and Mitochondria-Mediated Apoptosis in Human Cancer Cells, 10.1021/jm4001665
  48. Zanoni Kassio P. S., Kariyazaki Bruna K., Ito Akitaka, Brennaman M. Kyle, Meyer Thomas J., Murakami Iha Neyde Y., Blue-Green Iridium(III) Emitter and Comprehensive Photophysical Elucidation of Heteroleptic Cyclometalated Iridium(III) Complexes, 10.1021/ic500070s
  49. Castor Katherine J., Metera Kimberly L., Tefashe Ushula M., Serpell Christopher J., Mauzeroll Janine, Sleiman Hanadi F., Cyclometalated Iridium(III) Imidazole Phenanthroline Complexes as Luminescent and Electrochemiluminescent G-Quadruplex DNA Binders, 10.1021/acs.inorgchem.5b00921
  50. Deraedt Quentin, Loiseau Frédérique, Elias Benjamin, Photochemical Tuning of Tris-Bidentate Acridine- and Phenazine-Based Ir(III) Complexes, 10.1007/s10895-016-1904-2
  51. Chen Yan-Min, Zhang An-Guo, Liu Yan-Ju, Wang Ke-Zhi, Synthesis, spectrophotometric pH titrations and DNA binding properties of a cyclometalated iridium(III) complex of tetrapyrido[3,2-a:2′,3′-c:3″,2″-h:2‴,3‴-j]phenazine, 10.1016/j.jorganchem.2010.12.013
  52. Rachford Aaron A., Ziessel Raymond, Bura Thomas, Retailleau Pascal, Castellano Felix N., Boron Dipyrromethene (Bodipy) Phosphorescence Revealed in [Ir(ppy)2(bpy-C≡C-Bodipy)]+, 10.1021/ic901996u
  53. Sun Yali, Chen Zhuo, Puodziukynaite Egle, Jenkins Dustin M., Reynolds John R., Schanze Kirk S., Light Harvesting Arrays of Polypyridine Ruthenium(II) Chromophores Prepared by Reversible Addition–Fragmentation Chain Transfer Polymerization, 10.1021/ma202804u
  54. Kolganova Natalia A., Florentiev Vladimir L., Chudinov Alexander V., Zasedatelev Alexander S., Timofeev Edward N., Simple and Stereoselective Preparation of an 4-(Aminomethyl)-1,2,3-triazolyl Nucleoside Phosphoramidite, 10.1002/cbdv.201000047